In 1985, he began his comedy career by following up on a suggestion by David Lawrence (a disc jockey friend who had been paying Drew to write jokes for David's radio show in Cleveland) to go to the library and borrow books on how to write jokes.[5][6] The following year, after winning an open-microphone contest, he became Master of Ceremonies at the Cleveland Comedy Club.[2] He performed at comedy clubs over the next few years in Cleveland and Los Angeles. He was first brought to the national eye as a comedian when he competed in the 1988 Star Search.[7] Carey was working as a stand-up comedian when he appeared on The Tonight Show Starring Johnny Carson in November 1991.[8] His performance that night impressed Carson, who invited Carey to the couch next to his desk; this was considered a rare honor for any comedian.[5][9] In that same year, Carey joined the 14th Annual Young Comedians Special on HBO and made his first appearance on Late Night with David Letterman.[10] In 1994, Carey wrote his own stand-up comedy special, Drew Carey: Human Cartoon, which aired on Showtime and won a CableACE Award for Best Writing.[11]

His early stand-up career led to supporting roles on television shows, during which he developed the character of a hapless middle-class bachelor. In 1993, Carey had a small role in the film Coneheads as a taxi passenger. In 1994, Carey co-starred with John Caponera in The Good Life, a short-lived sitcom on NBC.[12] After the show was cancelled, Bruce Helford, a writer on the show, hired Carey as a consultant for the television show Someone Like Me.[13]

After their stint on Someone Like Me, Carey and Helford developed and produced the storyline for The Drew Carey Show. The sitcom revolved around a fictionalized version of Carey, as he took on the stresses of life and work with his group of childhood friends. The show premiered on September 13, 1995 on ABC. In his autobiography, Carey revealed his frustration with having to deal with censors and being unable to employ the off-color humor common in his stand-up routines.[4] Carey initially earned $60,000 per episode in the first seasons, then renegotiated for $300,000.[14] By the final season, he was earning $750,000 per episode.[15] The show had high ratings for its first few seasons, but declining ratings and increasing production costs (around $3 million per episode) precipitated its cancellation.[15][16] The program had a total of 233 episodes over its nine-year run and Carey was one of four actors to appear in every episode. The show starred (in order of episode appearances) Carey, Diedrich Bader, Kathy Kinney, Ryan Stiles (all in every episode); Craig Ferguson (starring role in seasons 2–8 and guest appearances in 9); Christa Miller (seasons 1–7); and Ian Gomez (semi-regular from seasons 1–9) and John Carroll Lynch (semi-regular from seasons 3/4–9).

While still starring in The Drew Carey Show, in 1998 Carey began hosting the American version of the improvisational comedy show Whose Line Is It Anyway?. He would announce the improv guests, direct the games, and then would usually involve himself in the final game of the episode. The show ran for a total of 220 episodes until the show's cancellation in 2006. In 1998, the New York Friars' Club made Carey the newest inductee of the group's Comedy Central Roast. His friend Ryan Stiles (who costarred in The Drew Carey Show and Whose Line Is It Anyway?) served as the roastmaster.[17] Carey's income from Whose Line Is It Anyway? and The Drew Carey Show led to his inclusion on the Forbes list of highest-paid entertainers of 1998, at 24th with $45.5 million.[18]

For the WB's 2004–2005 prime time schedule, Carey co-produced and starred in Drew Carey's Green Screen Show, a spin-off of Whose Line Is It Anyway?.[19] It was canceled by the WB, but picked up shortly afterward by Comedy Central.[20] The show's premise relied on the use of a green screen for all of the actors' improv interactions. Animation on the screen was inserted during post-production.

In April 2011, Carey began hosting a new primetime improv show, called Drew Carey's Improv-A-Ganza. It was filmed at the MGM Grand in Las Vegas, Nevada and first aired on April 11.[21] The show takes on the premise of Whose Line? and Drew Carey's Green Screen Show in that it features many of the same performers from both shows and they do improv based on audience-provided suggestions.

Carey was one of the founders of the Improv All-Stars, a group of eleven actors who perform in unscripted skits.[22] The group joined Carey in all three of his improv shows, Whose Line Is It Anyway?, Drew Carey's Green Screen Show, and Drew Carey's Improv-a-ganza and some members had major roles or guest starred on The Drew Carey Show.[23] The Improv All-Stars travel on comedy tours, performing at comedy clubs throughout the United States.

Beginning in 2007, Carey began hosting game shows, beginning with his April selection as host of the CBS game show pilot Power of 10. The show ran from August 7, 2007 to April 7, 2008 and aired twice weekly during the late summer and early fall. Each game featured contestants predicting how a cross-section of Americans responded to questions covering a wide variety of topics in polls conducted by CBS.[24]

After taping the pilot episode for Power of 10, Carey was contacted by CBS about replacing Bob Barker—who had earlier announced his own retirement—as host of The Price Is Right. After initially turning down the offer, Carey announced on Late Show with David Letterman that he would succeed Barker as host of the program beginning in the fall of 2007.[25] His first episode of The Price Is Right was taped on August 15, and his shows began airing on October 15. In response to replacing Barker as host of the game show, Carey stated "You can't replace Bob Barker. I don't compare myself to anybody... It's only about what you're doing and supposed to do, and I feel like I'm supposed to be doing this."[26] When Carey began hosting, the set, theme music, and show logo were updated. However, Carey kept the old closing line about spaying and neutering the pets that originated with Barker, although his version uses slightly different wording. During Carey's second year as host, he began to write some of the sketches used during the Showcase, which sometimes features guest appearances by stars of other CBS programs. In the April Fools' Day 2013 episode, Carey and announcer George Gray switched places with the models, letting the two men be the models for the episode.

Disney's Hollywood Studios (then "Disney-MGM Studios"), part of Walt Disney World Resort in Florida, debuted a 12-minute attraction in 1999 titled Sounds Dangerous!.[28] In the show, a camera follows Carey through a day as an undercover detective. When his video camera fails, the audience is left in complete darkness wearing earphones, following his adventure through sound cues. The attraction is now closed.

In 2000, Carey was given a cameo appearance in the House Party expansion pack of the computer game The Sims.[29] To make him appear, the characters in the game must throw a successful party, which causes Carey to arrive in a limo and join the festivities. Carey is a fan of The Sims series and during one April Fool's episode of The Drew Carey Show, a scene takes place completely within The Sims.[29][30] Carey made several other cameo appearances in music videos, including "Weird Al" Yankovic's "It's All About the Pentiums"[31] and Fountains of Wayne's 2004 video for "Mexican Wine", giving an introduction to the video as if it were on a stage.[32]

Although primarily known for his television work, Carey has done limited film work, with his first appearance in 1993's Coneheads. His next film was the 2000 television film, Geppetto that debuted on The Wonderful World of Disney. The film, an adaptation of Pinocchio, included actor Wayne Brady who had joined Carey on his improv shows.[33] Carey took singing lessons to prepare for the role.[3] In 2005, Carey appeared in three films: the animated film Robots, where he provided a voice-over for the character Crank; The Aristocrats where he retold a dirty joke along with other celebrities; and the documentary, Fuck, where he was interviewed.

Carey provided the entertainment for the 2002 Annual White House correspondents' dinner.[10] Once Carey completed his standup routine for the 1,800 guests, President George W. Bush, noting Carey's improv work, made a joke of his own: "Drew? Got any interest in the Middle East?"[34] In 2003, he joined Jamie Kennedy to host the WB's live special Play for a Billion.[35] In September 2003, Carey led a group of comedians, including Blake Clark and The Drew Carey Show's Kathy Kinney, on a comedy tour of Iraq.[36]

Carey has routinely written throughout his career, including developing his stand-up comedy routines in his early stand-up career, and then moving on to assist in writing sitcoms. In 1997, Carey published his autobiography, Dirty Jokes and Beer: Stories of the Unrefined wherein he shared memories of his early childhood and of his father's death when he was eight. He also revealed that he was once molested, had suffered bouts of depression, and had made two suicide attempts by swallowing a large amount of sleeping pills.[4] The book discusses his college fraternity years while attending Kent State University, and his professional career up to that time. The book featured large amounts of profanity and, as the title suggests, includes multiple dirty jokes (there is one at the start of each chapter) and references to beer. The book was featured on The New York Times bestseller list for three months.[38]

He adopted his crew cut hair style while serving in the United States Marine Corps. Carey has had refractive surgery to correct his vision and therefore did not really require glasses (any glasses he wore in public were merely props to help the audience recognize him).[39] However, while this was true for several years, on the May 17, 2006 episode of Jimmy Kimmel Live! he revealed that when he turned 40, he actually developed a need for bifocals. As of 2007, Carey resides in Los Angeles and New York City.[40]

Carey is a father figure to Nicole Jaracz's son, Connor, from a previous relationship. They have no children together. Nicole and Connor have appeared alongside Carey on The Price Is Right several times.[41] Although he proposed to Jaracz in 2007, the pair never wed as the engagement was called off in January 2012.[42][43]

After suffering chest pains while filming The Drew Carey Show in August 2001, Carey went to the hospital where he underwent a coronary angioplasty.[44] Although his weight was a comedic topic throughout his sitcom and improv shows, in 2010 he began a diet and exercise plan, resulting in an extensive weight loss (similar to former TPIR announcer Rod Roddy). He also claimed that he cured his Type 2 diabetes.[45]

Carey is an outspoken libertarian.[46][47][48][49] He has expressed his political philosophy in the following terms, "I believe the answers to all the problems we face as a society won't come from Washington, it will come from us. So the way we decide to live our lives and our decisions about what we buy or don't buy are much more important than who we vote for."[50]

Carey has spoken about his various political beliefs in several interviews, and in 1998 he led a "smoke-in" in defiance of California's newly passed no-smoking ordinance inside bars and restaurants.[53] Carey has hosted a series of mini-documentaries called The Drew Carey Project on Reason.tv, an online project of Reason Foundation, a libertarian think tank.[54] The first episode, "Gridlock", addresses private highway ownership and was released on October 15, 2007. Other episodes discuss topics such as eminent domain, urban traffic congestion, and medical marijuana. Carey also sits on the board of trustees of the Reason Foundation, a libertarian-oriented nonprofit organization.[55]

Carey has shown his support for the Indians by throwing the first pitch at an August 12, 2006, game against the Kansas City Royals. He was rewarded by the Cleveland Indians for being "the greatest Indians fan alive" with a personal bobblehead doll made in his likeness that was given to fans. Carey responded to his bobblehead likeness by saying "Bobblehead Day, for me, is as big as getting a star in the Hollywood Walk of Fame."[58]

In 2001, Carey was the first television actor to enter World Wrestling Federation's 30-man "Royal Rumble" match, which he did to promote an improv comedy pay-per-view at the time. He appeared in a few backstage segments before his brief participation in the match. Upon entering the ring, Carey stood unopposed for more than half a minute, but after the next entrant Kane refused a monetary bribe, Carey eliminated himself from the match by jumping over the top rope and retreated from ringside.[59] On April 2, 2011, Carey was inducted into the WWE Hall of Fame by Kane.[60]

Carey competed against five other celebrities in the first celebrity edition of the 2003 World Poker Tour. He placed fifth, only beating out actor Jack Black. Carey won $2,000 for his charity.[61]

On May 15, 2011, Carey completed the "Marine Corps Historic Half Marathon" in 1:57:02, then on September 4, 2011, he improved to complete the Disneyland Half Marathon in 1:50:46. And on October 30, 2011, he finished the Marine Corps Marathon with a chip time of 4:37:11, placing 10149th out of 20940.

Carey is a supporter of libraries, crediting them for beginning his successful comedy career. On May 2, 2000, in a celebrity edition of Who Wants to Be a Millionaire, he selected the Ohio Library Foundation to receive his $500,000 winnings.[62] He later went on to win an additional $32,000 on the second celebrity Millionaire, making him one of the biggest winning contestants on Millionaire who did not win the top prize. Carey also has played on the World Poker Tour in the Hollywood Home games for the Cleveland Public Library charity.[63] In June 2007, Carey offered to donate up to $100,000 (in $10,000 increments) to the Mooch Myernick Memorial Fund if anybody could beat him at the video game FIFA Soccer 07 for the Xbox 360. He dared five players from both the U.S. Men's and Women's National Teams to compete against him.[64] Carey ended up donating $100,000 plus $60,000 for losing two games out of the six games he played.[65]

In October 2009, Carey made a bid of $25,000 in a charity auction for the @drew Twitter account. He later increased his offer to $100,000 if the number of followers of his account @DrewFromTV reached 100,000 by the end of the auction.[66] In an interview with CBS News, he said he would instead donate $1 million to the charity Livestrong Foundation if his follower count reached one million by December 31, 2009.[67]

Carey can sometimes be seen on the sidelines of U.S. National Team soccer games as a press photographer.[68] His images are sold via wire services under the pseudonym Brooks Parkenridge.[57] He was at the 2006 FIFA World Cup in the summer of 2006, for his television show Drew Carey's Sporting Adventures.